Use of alkylglycoside sulfosuccinates for the production of cosmetic preparations and cleaning agents

ABSTRACT

The invention relates to alkylglycoside sulfosuccinates of the general formula (1) defined herein, useful in cosmetic preparations.

The invention relates to the use of alkoxylated sulfosuccinatescontaining ester groups and based on alkyl glycosides for the productionof mild cosmetic preparations and aqueous compositions which containthese compounds.

Cosmetic preparations, in particular those which come within the area ofhair and body cleaning, such as shower baths, foam baths, hair shampoos,baby shampoos, baby baths and liquid soaps, contain as cleaningcomponents mainly anionic surfactants such as carboxylates, alkylsulfates and alkyl ether sulfates.

These preparations should clean the skin surface, preferably only thefilm adhering to it, which can consist of body secretions such asperspiration and fats, flakes of skin or deposited dirt from theenvironment. The cleaning agents should in no case dry out the skin,irritate it or impair its natural function.

As the preparations can lead, however, during their frequent--in recentyears almost daily--use to irritations of the skin, use is frequentlyadditionally made, in order to improve the skin and eye mucosacompatibility, of so-called mild surfactants such as, for example,betaines, protein derivatives, ampholytes, alkyl ether carboxylates andsulfosuccinates.

Especially for baby care agents and baby shampoos and preparations forsensitive skin, particular value is placed on extremely low contents ofsubstances irritating the skin and eye mucosa. The anionic surfactantsconventionally used because of their excellent cleaning and foam-formingproperties can be rendered substantially milder in their irritant actionby means of the known mild cosurfactants, but in practice improvements,in particular in the way of eye mucosa compatibility, are stillrequired.

In high concentrations or on their own, the mild surfactants aresubstantially irritation-free, but then do not have foaming and cleaningproperties suitable for practical use and have unsatisfactoryviscosities.

A further criterion for the usefulness of the surface-active substancesis their toxicity. The toxicity lies in the surfactants themselves orproducts thereof formed by interaction with other constituents of theformulation.

As a result of increased environmental awareness, products areadditionally required which are based on natural, renewable rawsubstances, have no toxicity whatsoever and can be rapidly andcompletely degraded in municipal sewage plants without toxicintermediates.

GB Patent 2,011,462 discloses polyalkoxylated monoand dicarboxylates ofc-methylglucosides, the only surfactant disclosed being GLUCAMATE®SSE-20 from Amerchol--a mixture of the mono- and distearates ofα-methylglucoside. It is used in skin-compatible preparations forremoving make-up from the eyes.

German Published Specification 3,336,760 describes mixtures of at leastone oligomeric alkyl- glucoside ether containing an alkyl radical having8-10 carbon atoms, ethoxylated methylglucoside dioleate, alkyl- orhydroxyalkyl polyglycosides containing an alkyl radical having 11-18carbon atoms and between 3-25 glycoside units and at least one nonionicpolymer from the group comprising the alkyl celluloses, polyhydroxyalkylcelluloses, poly-β-alanines and polyvinylpyrrolidone as mild hair- andbody-cleaning agents.

In practice, high molecular weight compounds sometimes exhibitapplication problems: they are very often difficult to dissolve in waterand necessitate a relatively large effort to disperse them in water;occasionally it is difficult to obtain the desired viscosity immediatelyor the formulations tend to be "stringy" and produce a sticky feeling onthe skin. Some of these disadvantages can be due to preparation andcould possibly be overcome by appropriate apparatus measures and carefulmonitoring of the course of the process.

The object of the present invention is to overcome these disadvantagesof the prior art and to make available mild, skin-compatible cosmeticpreparations, in particular those which come within the area of hair-and body-cleaning.

This object is achieved by alkoxylated sulfosuccinates containing estergroups and based on alkyl glycosides additionally used according to theinvention. The invention therefore relates to the use of alkylglycosidesulfosuccinates of the general formula (1) ##STR1## wherein R¹ is H or alinear, saturated or unsaturated hydrocarbon radical having 1-18,preferably 1-10, in particular 1-4 carbon atoms and x is 0-10,preferably 0-5, and R is attached at the 1-position;

each R² is the same or different and is a linear, saturated orunsaturated acyl radical having 8-22 carbon atoms, preferably 12-18 orcan be selected from the group consisting of natural coconut fatty acidsacyl radicals carbon atoms;

each R³, independently of one another, is H or the radical [CO--CH(SO₃⁻)--CH₂ --COO⁻ ]·mM, provided that R₃ is said radical at least once ineach G;

each R⁴, independently of one another, can be H or CH₃ ;

n is 1 to 10, preferably 1 to 6 and more preferably 1 to 3;

the sum of (a+b+d) or each unit G is 1-20, preferably 1-10, and morepreferably 1-3, and c is 1-5; and

each M is the same or different and is a cation of an alkali metal or analkaline earth metal, ammonium, or H⁺, wherein m equals 2 divided by thevalence of M; and

wherein, when n is greater than 1, each G is attached to adjacent Ggroups at the 1,2-; 1,3-; 1,4- or 1,6-positions;

and

said compounds in the production of cosmetic preparations and cleaningagents.

The invention further relates to aqueous preparations containing

A) 5-20% by weight of at least one compound according to the generalformula (1) as defined above;

B) 1-5% by weight of at least one thickener;

C) 0-10% by weight of an electrolyte salt;

D) 0-10% by weight of customary auxiliaries and additives; and

E) 55-94% by weight of water.

Further embodiments of the invention are characterized by the claims.

One starting substance for the preparation of the compounds of thegeneral formula (1) according to the invention are commercial monomersand oligomers of glucose, for example glucose syrup from Cerestar.

The degree of polymerization of the glucose varies according to theprocess and manufacturer and is in the range 1-10, such that n asdefined above is 1-10. The compounds useful according to the inventioninclude mixtures of compounds having these various degrees ofpolymerization. Although the maximum degree of polymerization n is about10, the largest part in any composition preferably has a degree ofpolymerization (n) of less than 5. The mean value of n can thereforealso be a decimal number, that is to say lie between two integers.

Thus, it will be recognized that the degree of polymerization n ofcompounds in formulations claimed according to the invention representsan average; that is, if n is defined as being in the range of 1 to 6 thecomposition can also comprise the comparatively small amounts ofcompounds in which n is greater than 6. Preferred compounds of formula(1) according to the invention have degrees of polymerization n lessthan or equal to 3 and in particular 1-2 with an average preferablyabout 1-1.5.

These glycosides are, in a first step, etherified or transetherified bygenerally customary processes (cf. U.S. Pat. No. 4,704,453,EP-A-0,301,298).

The group R of the glycoside is preferably an alkyl group having 1-10,preferably 1-4 carbon atoms or an alkenyl group having 2-10, preferably2-4, carbon atoms. The group R can optionally be replaced by highergroups having up to 18 carbon atoms. R can furthermore be a polyethergroup of the structure --(CH₂ --CH₂ --O--)_(x) --R¹, in which R¹ is H oran alkyl or alkenyl group as described above for R and x can assumevalues between 1-10, preferably 1-5.

In a second step the acylation reaction of one mol of fatty acid orfatty acid methyl ester or fatty acid ethyl ester respectively iscarried out per glycoside unit. Instead of the fatty acids or theirmethyl or ethyl esters, the natural fats and oils, that is to say theirglycerol esters, can also be employed.

The fatty acids used are the monobasic acids having 8-22 carbonatoms--preferably the naturally occurring acids --such as lauric acid,myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid,linolenic acid, ricinoleic acid, coconut fatty acid or their mixtures(compare J. Am. Oil Chemists' Soc. 38, 517-520 (1961) and EP-A0,190,779). The glycoside esters are alkoxylated, preferably ethoxylatedor propoxylated, by processes known per se (J. Am. Oil Chemists' Soc.38, 517-520 (1961), U.S. Pat. No. 3,640,998). The ethoxylation orpropoxylation can also be carried out before the introduction of theester function. The amounts of ethylene oxide and/or propylene oxide arechosen to provide the desired number of alkoxy (ethoxy and propoxy)units in the molecule, as defined above. Preferably, the rate ofaddition is between 1 and 20 alkoxy units in total per repeatingglycoside unit, values according to the invention preferably beinggreater than 5, in particular 8-20 alkoxy units per unit.

The reaction to give the sulfosuccinate is carried out with maleicanhydride and subsequent sulfonation with sodium sulfite according toprocesses known per se (compare German Published Specification2,700,072). Reaction is carried out in this case with one mol of maleicanhydride per mol of hydroxyl group to be reacted at 60°-80° C. untilthe reaction is complete. The maleic acid hemiester is then added to anaqueous sodium sulfite solution (1 equivalent of sulfite per equivalentof hemiester) and sulfonated at 60°-80° C. until the sulfite hascompletely reacted. The aqueous product is then adjusted to neutral pH.

While commercial sulfosuccinates can only be dissolved in water inconcentrations up to about 40% by weight, the compounds according to theinvention surprisingly have the advantage that they can be prepared inconcentrations of 50% by weight and higher as clear, low-viscositysolutions.

These compounds, which can be additionally used on their own or in amixture, can be employed in concentrations of 5-20, preferably of 6-12%by weight, relative to the total mixture.

The number of anionic groups in the molecule is affected by the mannerin which the glycoside molecules are linked to one another. If theglycoside rings are linked to one another in the 1,4- or 1,3-position,it is simpler for steric reasons to substitute all the hydroxyl groupsthan if the linkage is effected in the 1,6- or 1,2-position. By way ofdefinition, and referring to the foregoing depiction of the ringstructure denoted as G, the carbon atoms in the ring are numberedconsecutively as 1 through 6, and the linkage through --O-- which formsthe ring is between the carbon atoms in positions 1 and 5.

Although theoretically 2n+1 anionic groups can be introduced into theglycoside ester, 2n to n groups are preferred according to theinvention.

The mixtures according to the invention are in general aqueouscompositions or aqueous alcoholic solutions, creams, emulsions or gelsand can still contain the auxiliaries and additives customary in eachcase for adaptation to the intended application and which, apart from inaqueous cleaning agents, such as mild washing-up liquids used by hand,are in particular additionally used for the production of cosmeticpreparations in the area of hair- and body-cleaning, that is to say forshower baths, foam baths, shampoos, liquid soaps, baby care agents andbaby detergents.

These are foam stabilizers such as polysaccharides, carboxyvinylpolymers, polyvinylpyrrolidones, fatty acid partial glyceride polyglycolethers, protein-fatty acid condensates; pearl luster and clouding agentssuch as fatty alcohols, ethylene glycol distearates, monoesters ofpolyhydric alcohols with higher fatty acids, polystyrene emulsions;complexing agents or sequestering agents such as salts ofethylenediaminetetraacetic acid; preservatives such as sorbic acid,citric acid, ascorbic acid, chlorhexidine, 8-hydroxyquinoline and itssalts, benzalkonium chloride, dimethylalkylbenzylammonium chloride andsmall amounts of fragrances, colorants, skin cosmetic active substances,vegetable extracts and buffer substances.

Thickeners additionally used according to B) can according to theinvention be any material which effectively thickens the formulation.Preferred thickeners include commercial fatty acid partial glyceridepolyglycol ethers such as REWODERM® LI 420, REWODERM® LI 48 (trademarkof REWO Chemische Werke GmbH, Steinau an der Straβe) in amounts from 1to 10, preferably from 2 to 4% by weight, relative to the total mixture.

Suitable electrolyte salts are all alkali metal, alkaline earth metaland ammonium salts which are soluble at 20° C. in amounts of at least 1%by weight. Those preferred are sodium chloride, magnesium chloride andammonium chloride, which can be additionally employed in amounts up toabout 10% by weight, preferably 1-5% by weight, relative to the totalformulation.

The content of wash-active substance (B-WAS) given in the followingexamples is titrated by the customary two-phase titration withbenzalkonium chloride against Methylene Blue as indicator (cf. S. R.Epton, Nature (London), 160, 1967, p. 795).

The hydrolysis number is a measure of the free and bound acids containedin fats and technical fatty acids. It gives the number of milligrams ofpotassium hydroxide which are necessary to hydrolyze 1 gram of substanceor technical fatty acids (mg of KOH/g). The values are determined by thestandard methods of the German Society for Fat Chemistry (DGF): DGFC-V3.

The hydroxyl value is used to determine the content of hydroxyl groupsand gives the number of milligrams of potassium hydroxide which arenecessary to neutralize the acetic acid consumed by 1 gram of substanceduring the acetylation (mg of KOH/g) The values are determined by theDGF standard method DGF C-V17A.

The solids content is determined by drying to constant weight at 105° C.

Preparation of the compounds according to the invention Example 1Preparation of butylglucoside coconut fatty acid ester

8 g of K₂ CO₃ was added to 826 g (3.5 mol) of n-butylglucoside and thereaction mixture was heated to 120° C. 750 g of coconut methyl ester wasadded dropwise to the reaction mixture at 50 mbar over the course of 2 hand was then reacted for 4 h at 120° C. and 30 mbar. The resultingmethanol was immediately removed by distillation during the course ofthis. A yellow, highly viscous material having the following analyticaldata resulted:

    ______________________________________                                        Hydrolysis value    110 mg of KOH/g                                           Hydroxyl value      430 mg of KOH/g                                           ______________________________________                                    

Example 2 Preparation of the polyethylene oxide ether

463 g of (1.05 mol) of butylglucoside ester from Example 1 were treatedwith 2.3 g of KOH and treated in portions with 464 g (10.5 mol) ofethylene oxide at 120° C. in an autoclave so that the pressure was atmost 5 bar. A highly viscous yellow material having the followinganalytical values resulted:

    ______________________________________                                        Hydrolysis value     54 mg of KOH/g                                           Hydroxyl value      223 mg of KOH/g                                           ______________________________________                                    

Example 3 Preparation of the sulfosuccinate

258 g (0.3 mol) of butylglucoside ester ethoxylate from Example 2 wasstirred with 57.6 g (0.6 mol) of maleic annydride at 70° C. for 2 h. Themaleic acid hemiester was then added to a solution of 350 g of water at60° C. containing 74.1 g (0.6 mol) of Na₂ SO₃ and stirred at thistemperature until the SO₂ content of the solution was <0.01%. A clearsolution having a 48.3% solids content and 43.5% Benzavlon washactivesubstance (B-WAS) resulted.

The following examples were carried out following Examples 1-3.

Example 4

258 g (0.3 mol) of butylglucoside ester ethoxylate from Example 2 wasreacted as described in Example 3 with 29 g (0.3 mol) of maleicanhydride and then sulfonated in a solution of 300 g of water containing37 g (0.3 mol) of Na₂ SO₃. The solution had a solids content of 49% anda B-WAS of 41%.

Example 5

258 g (0.3 mol) of butylglucoside ester ethoxylate from Example 2 wasreacted as described in Example 3 with 87 g (0.9 mol) of maleicanhydride and then sulfonated with a solution of 400 g of watercontaining 111 g (0.9 mol) of Na₂ SO₃. The solution had a solids contentof 47% and a B-WAS of 43%.

Example 6

200 g (0.3 g mol) of butylglucoside ester ethoxylate (prepared as inexample 2, except that the mole ratio of ethylene oxide:ester was 5:1)was reacted with 59 g (0.6 mol) of maleic anhydride at 80° C. Asdescribed in Example 1, the hemiester was then sulfonated in a solutionof 330 g of water and 77 g (0.61 mol) of Na₂ SO₃. The sulfosuccinate had49% solids and a B-WAS of 41%.

Example 7

200 g (0.3 mol) of the butylglucoside ester ethoxylate as described inExample 6 was reacted with 88.5 g (0.9 mol) of maleic anhydride at 80°C. Analogously to Example 3, the sulfonation was carried out in 400 g ofwater and 116 g of Na₂ SO₃. The sulfosuccinate had 50% solids and aB-WAS of 44%.

Example 8

200 g (0.3 mol) of butylglucoside ester ethoxylate as in Example 6 wasreacted with 29.5 g (0.3 mol) of maleic anhydride at 75° C. Analogouslyto Example 3, sulfonation was carried out in 270 g of water containing38 g (0.3 mol) of Na₂ SO₃. The sulfosuccinate had 48.2% solids togetherwith 28.1% B-WAS.

Example 9

220 g (0.5 mol) of butylglucoside ester from Example 1 was reactedanalogously to Example 3 with 49 g (0.5 mol) of maleic anhydride andthen sulfonated in 500 g of water containing 63 g (0.5 mol) of Na₂ SO₃.The sulfosuccinate had 38.3% solids and a B-WAS of 23.2%.

Example 10

238 g (1 mol) of butylglucoside was treated with 0.5 g of potassiumhydroxide and treated in portions with 440 g (10 mol) of ethylene oxideat 140° C. in an autoclave so that the maximum pressure did not exceed 5bar. A viscous, yellow product having a hydroxyl value of 360 resulted.

Example 11

678 g (1 mol) of the product from Example 10 was treated with 3 g of K₂CO₃ and heated to 120° C. under an N₂ atmosphere. Under a vacuum of 100mbar, 210 g (0.95 mol) of coconut methyl ester was added dropwise to thereaction solution over the course of about 2 h and the mixture was thenreacted for a further 4 h at 120° C. The resulting methanol wascontinuously removed from the system. A pale-yellow, viscous materialhaving the following analytical values resulted:

    ______________________________________                                        Hydrolysis value  60                                                          Hydroxyl value   240                                                          ______________________________________                                    

Example 12

890 g (1 mol) of butylglucoside ethoxylate ester from Example 11 wasreacted as described in Example 3 with 98 g (1 mol) of maleic anhydrideand then sulfonated with a solution of 1100 g of water and 126 g of Na₂SO₃. A pale solution having a solids content of 49% and a B-WAS of 31%resulted.

                                      TABLE 1                                     __________________________________________________________________________    Example                                                                            R   R.sup.2                                                                              R.sup.3      R.sup.4                                                                         Σ                                                                         d    n                                       __________________________________________________________________________     1*  n-butyl                                                                           coconut acyl                                                                         3 × H  H  0                                                                              0    about 1.3                                2*  n-butyl                                                                           coconut acyl                                                                         3 × H  H 10                                                                              0    about 1.3                               3    n-butyl                                                                           coconut acyl                                                                         1 × H, 2 × sulfosuccinate                                                      H 10                                                                              0    about 1.3                               4    n-butyl                                                                           coconut acyl                                                                         2 × H, 1 × sulfosuccinate                                                      H 10                                                                              0    about 1.3                               5    n-butyl                                                                           coconut acyl                                                                         3 × sulfosuccinate                                                                   H 10                                                                              0    about 1.3                               6    n-butyl                                                                           coconut acyl                                                                         1 × H, 2 × sulfosuccinate                                                      H  5                                                                              0    about 1.3                               7    n-butyl                                                                           coconut acyl                                                                         3 × sulfosuccinate                                                                   H  5                                                                              0    about 1.3                               8    n-butyl                                                                           coconut acyl                                                                         2 × H, 1 × sulfosuccinate                                                      H  5                                                                              0    about 1.3                               9    n-butyl                                                                           coconut acyl                                                                         2 × H, 1 × sulfosuccinate                                                      H  0                                                                              0    about 1.3                               10*  n-butyl                                                                           H      3 × H  H 10                                                                              about 1-3                                                                          about 1.3                               11*  n-butyl                                                                           coconut acyl                                                                         3 × H  H 10                                                                              about 1-3                                                                          about 1.3                               12   n-butyl                                                                           coconut acyl                                                                         2 × H, 1 × sulfosuccinate                                                      H 10                                                                              about 1-3                                                                          about 1.3                               __________________________________________________________________________     Coconut acyl = mixture of natural C.sub.12-16 fatty acids                     * = Precursor materials                                                       Sulfosuccinate = --CO--CH(SO.sub.3 --)--CH.sub.2 --COO--2 Na.sup.+  or        --CO--CH.sub.2 --CH--(SO.sub.3 --)--COO--2                                    Σ = the sum of (a + b + c + d)                                     

All formulations are given in percent by weight calculated relative tosolids.

The following surfactants, when referred to herein, are referred to byterminology employed according to the Cosmetic, Toiletry and FragranceAssociation (CTFA).

    ______________________________________                                        Reference Number                                                              in Formulation Compound Name                                                  ______________________________________                                        1)             Disodium laureth sulfosuccinate                                2)             Sodium laureth sulfate                                         3)             Cocoamidopropyl betaine                                        4)             PEG-80 glyceryl tallowate                                      5)             Glyceryl stearate                                              6)             PEG-200 glyceryl tallowate mod.                                7)             Disodium cocoamphodiacetate                                    ______________________________________                                        Basic formulation: hair shampoo                                               Example 4 or 12    2-6      parts by weight                                   REWOPOL ® NL 3-28                                                                             6-15    "                                                 REWODERM ® LI S 75.sup.6)                                                                    1-3      "                                                 demin. water       to 100                                                     Basic formulation: baby shampoo or shampoo for sensitive skin                 Example 4 or 12    3-8      parts by weight                                   REWOTERIC ® AM 2 C NM.sup.7)                                                                  2-10    "                                                 REWOTERIC ® AM B 13 H.sup.3)                                                                 4-8      "                                                 REWODERM ® LI 48-50.sup.4)                                                                   1-4      "                                                 demin. water       to 100                                                     Basic formulation: cream                                                      Example 4 or 12    1-5      parts by weight                                   Glycerol monodistearate                                                                           2-10    "                                                 Cetyl alcohol      1-4      "                                                 Paraffin oil 3.5° E                                                                        4-12    "                                                 Glycerol           1-5      "                                                 demin. water       to 100                                                     Preservative       as required                                                 Basic formulation: shower bath                                               Example 4 or 12     2-10    parts by weight                                   REWOTERIC ® AM B 13                                                                          2-8      "                                                 REWOPOL ® NL 3-28                                                                             5-15    "                                                 REWODERM ® LI 48-50                                                                          1-4      "                                                 demin. water       to 100                                                     Basic formulation: washing-up liquid                                          Example 12         1-5      parts by weight                                   REWOPOL ® NL 3-28                                                                             1-30    "                                                 REWOTERIC ® AM CAS                                                                           1-5      "                                                 REWOPOL ® LA 6  1-10    "                                                 demin. water       to 100                                                     ______________________________________                                    

Application check Shower bath

The glycoside derivatives developed have been assessed in the testrecipe by a test panel of 20 persons (female and male) with respect to

foaming power, foam structure

feeling of the wet skin

feeling of the dried skin

for skin compatibility (zein values) compare: Z. Gotte"Hautvertraglichkeit von Tensiden, gemessen am Losevermogen fur Aein"(skin compatibility of surfactants, measured by dissolving power forzein) Chem. Phys. Appl. Surface Active Subst. Proc. Int. Congr. 4 (1964)83-90.

    ______________________________________                                        Assessment scheme:                                                                         <200 mg of N/100 ml = non-irritating                                          200-400 mg of N/100 ml = slightly                                             irritating                                                                    >400 mg of N/100 ml = irritating                                 ______________________________________                                    

Plate washing test 1. Principle

The number of artificially soiled plates which can be cleaned in awashing-up liquid solution until the liquor is exhausted is determined.

2. Production of the test soiling

2.0 parts by weight of technical oleic acid, 49.9 parts by weight ofwheatmeal flour and 0.1 part by weight of the dye Sudan Red aresuccessively stirred into a melt of 48.0 parts by weight of lard at 50°C. and homogenized.

3. Coating the plate

The plates are first washed, rinsed with clear water and additionallyrinsed with isopropanol. 2 g of the test soiling at 40° C. are thenuniformly distributed on each dried plate on the inner surface using abrush and then stored for 24 h at 20° C. and 65% relative atmospherichumidity.

4 Preparation of the washing liquors Washing liquor A

8 l of tap water at 50° C. having a German hardness (° dH) of 10° and acontent of the test substance to be checked of 0.02% by weight (relativeto solids) is placed in a bowl and stirred for 2 min with a bladestirrer at 300 rpm in such a way that sufficient foam results.

Washing liquor B

10 1 of cold tap water (20° C. 10° dH) which is continuously replaced byrunning fresh water (5 l/min) are placed in a second bowl.

5. Washing process

The soiled plates are washed in succession for 30 seconds each under thesurface of the washing liquor A using the washing brush. They are thenrinsed by simple immersion in liquor B. Washing is carried out untilliquor A is exhausted. This is recognized by the disappearance of thefoam, the visually recognizable remaining of soil particles on thewashed plates or the floating of black or red fat particles on thesurface of the liquor A.

6. Assessment

The number of plates washed perfectly clean is determined by subjectiveassessment of at least 3 persons. The following are stated:

    ______________________________________                                        Number of plates      as stated                                               Concentration of the washing                                                                        0.02% solids content                                    liquor in g/l                                                                 Water hardness in mmol of Ca.sup.++ /l                                                              10°dH                                            Washing temperature in °C.                                                                   50                                                      ______________________________________                                    

    ______________________________________                                        Shower Bath                                                                   Formulation 1          2          3                                           ______________________________________                                        Example 4   5          --         --                                          Example 12  --         5          --                                          REWOTERIC ®                                                                           3          3          3                                           AM B 13.sup.3)                                                                REWOPOL ®                                                                             11         11         16                                          NL 3-28.sup.2)                                                                REWODERM ®                                                                            2          2          2                                           LI 48-50.sup.4)                                                               demin. water                                                                              to 100     to 100     to 100                                      pH adjusted with                                                                          6.5        6.5        6.5                                         citric acid to                                                                Foaming power.sup.A)                                                                      good foam  good foam  good foam                                               development                                                                              development                                                                              development                                 Foam structure.sup.A)                                                                     creamy - soft                                                                            creamy - soft                                                                            having large                                                                  bubbles                                     Feeling - wet skin.sup.A)                                                                 creamy - soft                                                                            creamy - soft                                                                            soft                                        Feeling - dry skin.sup.A)                                                                 smooth - soft                                                                            smooth - soft                                                                            slightly dry                                ______________________________________                                         .sup.A) The assessment was carried out by a graded assessment system,         where the above mentioned assessment represents the arithmetic mean.     

    ______________________________________                                        Skin Cleaning                                                                 Preparation,                                                                  Reduction                                                                     of Zein Values                                                                            1        2        3      4                                        ______________________________________                                        Example 4   4.5               --     --                                       Example 12           4.5      --     --                                       REWOPOL ®                                                                             --       --       4.5    --                                       SB FA 30.sup.1)                                                               REWOPOL ®                                                                             10.5     10.5     10.5   15                                       NL 3-28.sup.2)                                                                demin. water                                                                              85       85       85     85                                       pH adjusted with                                                                          6.5      6.5      65     6.5                                      citric acid to                                                                Assessment of the                                                                         creamy   creamy   having having                                   foam quality                                                                              having   having   minute large                                                minute   minute   bubbles                                                                              bubbles                                              bubbles  bubbles                                                  Feeling after wash-                                                                       smooth,  smooth,  soft   somewhat                                 ing on the dry skin                                                                       soft     soft            rough                                    Zein values 120 mg   122 mg   270 mg 300 mg                                               of N/100 of N/100 of N/100                                                                             of N/100                                             ml       ml       ml     ml                                       ______________________________________                                    

Hair shampoo

The glycoside derivatives developed have been assessed in the recipe by10 volunteers experienced in application for:

Combability

Volume of the hair and hold of the hairstyle

    ______________________________________                                                      Formulation                                                                     1          2      3                                           ______________________________________                                        Example 4       4.5        --     --                                          Example 12      --         4.5    --                                          REWOPOL ® NL 3-28.sup.2)                                                                  10.5       10.5   15                                          REWODERM ® LI S 75.sup.6)                                                                 2          2      2                                           demin. water    83         83     83                                          pH adjusted with citric                                                                       6.5        6.5    6.5                                         acid to                                                                       Combability     5          6      2                                           Volume of the hair                                                                            6          5      3                                           Hold of the hairstyle                                                         ______________________________________                                        Assessment of combability:                                                    1-3     Difficult to comb through: the hair offers                                    considerable resistance to the combing process                        4-7     The hair can be combed through relatively easily,                             combing resistance is decreased, adequate for a                               conditioning shampoo depending on the hair type                       8-10    Reserved for the subsequent aftertreatment by so-                             called hair-rinse agents                                              Assessment of the hair volume and of the hold of the hairstyle                1-3     The hair is dry or dull and lifeless; poor hold of                            the hairstyle                                                         4-7     The hair is soft and bouffant at the same time                                together with a good hold of the hairstyle                            8-10    The hair is soft and smooth, but too loose, as a                              result the hairstyle does not hold well.                              ______________________________________                                    

The assessment was carried out by a graded point system, where theabovementioned assessment represents the arithmetic mean.

Skin cream

Use of aqueous sulfosuccinates based on glycoside as emulsifiers in O/Wemulsions

    ______________________________________                                        HLB value      Example 4     about 16                                                        Example 12    about 16                                         ______________________________________                                    

Determination according to W. C. Griffin ("Calculation of Surface ActiveAgents by HLB", Journal Soc. Cosm. Chem. 1, 311 (1949)).

    ______________________________________                                        Skin Cream                                                                    O/W Test                                                                      Formulation                                                                             1        2         3       4                                        ______________________________________                                        Example 4 2        --        --      --                                       Example 12                                                                              --       2         --      --                                       Stearyl alcohol                                                                         --       --        2       --                                       +3EO                                                                          REWOMUL ®                                                                           6        6         6       6                                        MG.sup.5)                                                                     REWOPOL ®                                                                           --       --        --      2                                        SB FA 30.sup.1)                                                               Cetyl alcohol                                                                           2        2         2       2                                        Liquid paraffin                                                                         8        8         8       8                                        3.5° E                                                                 Glycerol  3        3         3       3                                        Preservative                                                                            as re-   as required                                                                             as required                                                                           as required                                        quired                                                              demin. water                                                                            to 100   to 100    to 100  to 100                                   Stability of the                                                                        stable   stable    stable  instable                                 emulsion at                                                                   50° C., 20° C.                                                  and 40° C.                                                             Appearance                                                                              smooth   smooth    smooth  greasy,                                            white    white     white   emulsion                                           cream    cream     cream   breaks                                   ______________________________________                                    

Assessment of the properties on the skin by 10 volunteers; more than 80%assessed the stable test recipes 1 and 2

as easy to spread on the skin

as easily absorbed into the skin

the skin is smooth and soft, without becoming sticky and greasy. Thecomparison recipe No. 4 is not assessed the same and is furthermoreunstable.

    ______________________________________                                        Baby shampoo or hair and body shampoo for sensitive skin                                     Formulation                                                                   1      2        3                                              ______________________________________                                        Example 4        6        --       --                                         Example 12       --       6        --                                         REWOTERIC ® AM 2C NM.sup.7)                                                                6        6        6                                          REWOTERIC ® AM B 13.sup.3)                                                                 4        4        4                                          REWODERM ® LI 48-50.sup.4)                                                                 2        2        2                                          REWOPOL ® NL 3-28.sup.2)                                                                   --       --       6                                          demin. water     to 100   to 100   to 100                                     pH adjusted with citric                                                                        6.5      6.5      6.5                                        acid to                                                                       Zein values, mg of N/100 ml                                                                    <70      <70      about 150                                  Skin roughness according to                                                                    slight   slight   distinct                                   Padberg.sup.B)   rough-   rough-   rough-                                                      ening    ening    ening                                      ______________________________________                                         .sup.B) Testing of skin compatibility according to Padberg, J. Soc. Cosm.     Chem. 20, 719-728 (1969)                                                 

The formulation shown is a "non-irritating" washing solution only"slightly roughening" the skin. The assessment "slightly roughening" isthe lowest which can be obtained with surfactants by the method shown.

Assessment of skin roughness according to Padberg:

Grade 1 very slight roughening--does not differ from the blank area

Grade 2 slight roughening--% Padberg below 50

Grade 3 distinct roughening--% Padberg over 50

Grade 4 heavy roughening--does not differ significantly from the sodiumlauryl sulfate area (comparison substance)

    ______________________________________                                        Test Formulation: Skin-compatible washing-up agents for                       manual use                                                                               Formulation                                                                    1      2        3        4                                        ______________________________________                                        Example 12   --        3       1.5    --                                      REWOPOL ® NL 3-28.sup.7)                                                               18       18       18     18                                      REWOTERIC ® AM CAS.sup.3)                                                              1.5      --       1.5    --                                      REWOPOL ® LA 6.sup.4)                                                                  1.5      --       --      3                                      Water        to 100   to 100   to 100 to 100                                  Plate washing test                                                                         12       20       18     12                                      Number of plates                                                              Zein values  220      195      220    250                                     (skin compatibility)                                                          Foam height (mm) +                                                                         195/185  190/180  195/190                                                                              190/180                                 0.5 ml of                                                                     Olive oil +  190/180  190/180  195/185                                                                              190/180                                 1.0 ml of                                                                     Olive oil    190/185  190/180  190/180                                                                              190/180                                 ______________________________________                                    

What is claimed is:
 1. An alkylglycoside sulfosuccinate of the formula( 1) ##STR2## wherein R¹ is H or a linear, saturated or unsaturatedhydrocarbon radical having 1-18 carbon atoms and x is 0-10 and R isattached at the 1-position;R², and when n is greater than 1 each R², isindependently a linear, saturated or unsaturated acyl radical having8-22 carbon atoms; R³, and when n is greater than 1 each R³, isindependently H or the radical [CO--CH(SO₃ ⁻)--CH₂ --COO³¹ ]·mM,provided that R³ is said radical at least once in each G; R⁴, and when nis greater than 1 each R⁴, is independently H or CH₃ ; n is 1 to 10 thesum of (a+b+d) in each unit G is 1-20 and c is 1-5; and M, and when n isgreater than 1 each M, is independently a cation of an alkali metal oran alkaline earth metal, ammonium, or H⁺, wherein m equals 2 divided bythe valence of M; andwherein, when n is greater than 1, each G isattached to adjacent G groups at the 1,2-; 1,3-; 1,4- or 1,6- positions.2. An alkylglycoside sulfosuccinate as claimed in claim 1, whereinR isan alkyl radical having 1-4 carbon atoms; R², and when n is greater than1 each R², is an acyl radical selected from the group consisting ofnatural coconut fatty acid acyl radicals; and n is 1-2.
 3. A compound asclaimed in claim 1 wherein when n is greater than 1 each G group isconnected to an adjacent G group at the 1,4-position.
 4. Analkylglycoside sulfosuccinate as claimed in claim 1 wherein R¹ is H or alinear, saturated or unsaturated hydrocarbon radical having 1-10 carbonatoms.
 5. An alkylglycoside sulfosuccinate as claimed in claim 4 whereinR¹ has 1-4 carbon atoms.
 6. An alkylglycoside sulfosuccinate as claimedin claim 1 wherein x is 0-5.
 7. An alkylglycoside sulfosuccinate asclaimed in claim 1 wherein R₂ is a linear, saturated or unsaturated acylradical having 12-18 carbon atoms.
 8. An alkylglycoside sulfosuccinateas claimed in claim 1 wherein n is 1 to
 6. 9. An alkylglycosidesulfosuccinate as claimed in claim 8 wherein n is 1 to
 3. 10. Analkylglycoside sulfosuccinate as claimed in claim 1 wherein the sum of(a+b+c) on each G unit is 1-10.
 11. An alkylglycoside sulfosuccinate asclaimed in claim 10 wherein the sum of (a+b+c) on each G unit is 1-3.12. A compound as claimed in claim 1 wherein R¹ is H or a linearsaturated os unsaturated hydrocarbon radical having 1-10 carbon atoms, xis 0-5; R² is a linear, saturated or unsaturated acyl radical having12-18 carbon atoms; n is 1 to 6; and the sum of (a+b+c) on each unit Gis 1-10.
 13. A compound as claimed in claim 4 wherein R¹ is H or alinear, saturated or unsaturated hydrocarbon having from 1-4 carbonatoms; n is 1 to 3; and the sum of (a+b+c) on each unit G is 1-3.